Search Vacation Homes in Great Barrington

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 583 Vacation Homes in Great Barrington with updated reviews, rates, and availability.

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (69)
"The host was great and the property had everything we wanted and more. We will be back."
Lakefront Summer Spectacular in New England Just 2 Hours From NYC

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is SAR 446
SAR 582 total
includes taxes & fees
1 Jun - 2 Jun
Deluxe Queen Room with 2 Queen Beds

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (51)
"Great spot on the lake. Super quiet and relaxing."
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Home w/ Fire Pit, Near Downtown Hudson + Skiing!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Lovely time; great property with comfortable furniture!!"
Home w/ Fire Pit, Near Downtown Hudson + Skiing!

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

10.0 out of 10, Exceptional, (19)
"We stayed here for skiing over a holiday weekend. The place was *very* clean and Tara was very responsive to helping with the only issue we had (which was weather related and not related to the house). The house is well outfitted and they also left a few basics for us in the kitchen which was a nice touch."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

Pristine Home In Becket Woods

9.8 out of 10, Exceptional, (15)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (29)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House

Becket Home w/ 3-Season Porch: Walk to Lake Access

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a clean, quiet spot for a nice weekend getaway. "
Becket Home w/ 3-Season Porch: Walk to Lake Access

Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community

10.0 out of 10, Exceptional, (3)
"Comfortable, clean , easy. "
Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community

Mountain View Getaway

10.0 out of 10, Exceptional, (52)
"We had a wonderful wknd and the hosts thought of everything, kids had a great time and look forward to coming back."
Mountain View Getaway

Yacca House NEW Serene Retreat in Canaan

Yacca House NEW Serene Retreat in Canaan

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (20)
"The property was close to town and very cozy, clean & comfortable. Would highly recommend attention to the details was impressive."
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Stay Lakeside This Summer!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is SAR 376
SAR 2,173 total
includes taxes & fees
1 Jun - 2 Jun
CT Gate House Goshen CT, Gate House Goshen CT

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Comfortable and relaxing spot. Really pretty lake. Fun stuff for paddling around the lake."
Berkshire Lake at the Pillow, and EV!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in